Acylated 5-aminoisothiazoles with insecticidal properties, intermediate products and process for producing them

ABSTRACT

The present invention relates to novel acylated 5-aminoisothiazoles of the formula (I) ##STR1## in which R 1 , R 2 , R 3 , R 4  and Y have the meaning given in the description, processes for their preparation and their use for controlling animal pests.

This application is a 371 of PCT/EP96/04796 filed Nov. 4, 1996.

The present invention relates to novel acylated 5-aminoisothiazoles,processes for their preparation and their use for controlling animalpests.

It is already known that certain acylated 4-cyano-5-aminoisothiazoleshave insecticidal properties (cf., for example, EP-A 0 623 282).

However, the activity and range of action of these compounds are notalways completely satisfactory, especially when low amounts are appliedand at low concentrations.

Novel acylated 5-aminoisothiazoles of the formula (I) ##STR2## in whichR¹ represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy,alkylthio or optionally substituted cycloalkyl,

R² represents hydrogen, halogen, cyano, nitro, thiocyanato,alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio,alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl,halogenoalkylsulfonyl or thiocarbamoyl,

R³ represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl,alkylcarbonyl, alkylsulfonyl, in each case optionally substitutedarylcarbonyl, arylsulfonyl or arylalkyl or optionally substitutedcycloalkyl,

R⁴ represents optionally substituted aryl, optionally substitutedcycloalkyl or optionally substituted cycloalkenyl and

Y represents optionally substituted alkylene, alkenylene or alkylenoxy,

have now been found.

It has furthermore been found that the acylated 5-aminoisothiazoles ofthe formula (I) are obtained by a process in which

a) 5-aminoisothiazoles of the formula (II) ##STR3## in which R¹, R² andR³ have the above-mentioned meaning,

are reacted with acid halides of the formula (III)

    R.sup.4 --Y--CO--Hal                                       (III)

in which

R⁴ and Y have the above-mentioned meaning and

Hal represents halogen,

in the presence of a base and in the presence of a diluent; or

b) acylated 5-aminoisothiazoles of the formula (Ia) ##STR4## in whichR¹, R³, R⁴ and Y have the above-mentioned meaning,

(α) are reacted with a halogenating agent, if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or

(β) are reacted with a nitrating reagent, if appropriate in the presenceof a diluent,

or

c) β-amino-thiocrotonamides of the formula (IV) ##STR5## in which R¹, R⁴and Y have the above-mentioned meaning and

R²⁻¹ represents cyano or alkoxycarbonyl,

are cyclized with an oxidizing agent, if appropriate in the presence ofa diluent.

Finally, it has been found that the novel acylated 5-aminoisothiazolesof the formula (I) have highly pronounced biological properties, andabove all are suitable for controlling animal pests, in particularinsects, arachnids and nematodes, which occur in agriculture, inforestry, in the preservation of stored products and materials and inthe hygiene sector.

The formula (I) provides a general definition of the acylated5-aminoisothiazoles according to the invention.

Preferred substituents and ranges of the radicals listed in the formulaementioned above and below are explained in the following.

R¹ preferably represents C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl having 1to 5 identical or different halogen atoms, such as fluorine, chlorineand bromine atoms, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁-C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, or represents C₃ -C₆-cycloalkyl which is optionally substituted once to three times in anidentical or different manner by C₁ -C₄ -alkyl or halogen.

R² preferably represents hydrogen, halogen, cyano, nitro, thiocyanato,C₁ -C₄ -alkoxy-carbonyl, C₂ -C₄ -alkenyloxy-carbonyl, C₁ -C₄ -alkylthio,C₁ -C₄ -halogenoalkylthio having 1 to 5 identical or different halogenatoms, such as fluorine and chlorine atoms, C₁ -C₄ -alkylsulfinyl, C₁-C₄ -halogenoalkylsulfinyl having 1 to 5 identical or different halogenatoms, such as fluorine and chlorine atoms, C₁ -C₄ -alkylsulfonyl or C₁-C₄ -halogenoalkylsulfonyl having 1 to 5 identical or different halogenatoms, such as fluorine and chlorine atoms, or represents thiocarbamoyl.

R³ preferably represents hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkylhaving 1 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkyl-carbonyl, C₁-C₄ -alkylsulfonyl or phenylcarbonyl, phenylsulfonyl or benzyl, in eachcase optionally substituted in the phenyl ring once to three times in anidentical or different manner, possible substituents in each case beinghalogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₂ -halogenoalkyl having 1 to5 identical or different halogen atoms, such as fluorine and chlorineatoms, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂ -halogenoalkoxy having1 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, or C₁ -C₂ -halogenoalkylthio having 1 to 5 identical ordifferent halogen atoms, such as fluorine and chlorine atoms, orrepresents C₃ -C₆ -cycloalkyl which is optionally substituted once tothree times in an identical or different manner by C₁ -C₄ -alkyl orhalogen.

R⁴ preferably represents phenyl which is optionally substituted once tothree times in an identical or different manner, possible substituentsbeing halogen, nitro, cyano, C₁ -C₁₂ -alkyl, C₁ -C₁₂ -halogenoalkylhaving 1 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, C₁ -C₁₂ -alkoxy, C₁ -C₁₂ -halogenoalkoxy having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₁ -C₁₂ -alkylthio, C₁ -C₁₂ -halogenoalkylthio having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₂ -C₁₂ -alkenyl, C₂ -C₁₂ -halogenoalkenyl having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₃ -C₈ -cycloalkyl which is optionally substituted once to threetimes in an identical or different manner by C₁ -C₄ -alkyl or halogen,and phenyl, phenoxy, phenylthio, benzyl or benzyloxy, in each caseoptionally substituted once to three times in an identical or differentmanner by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkylhaving 1 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl, C₁ -C₄-halogenoalkylsulfonyl having 1 to 5 identical or different halogenatoms, such as fluorine and chlorine atoms, C₁ -C₄ -alkylcarbonyl, C₁-C₄ -alkoxy-carbonyl, thioamide, C₁ -C₄ -alkoximino-C₁ -C₄ -alkyl oroptionally C₁ -C₄ -alkyl-substituted oxdiazolyl,

or represents C₃ -C₈ -cycloalkyl or C₅ -C₈ -cycloalkenyl, in each caseoptionally substituted once to three times in an identical or differentmanner, possible substituents being C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkylhaving 1 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₃ -C₈ -cycloalkyl and phenyl which is optionally substitutedonce to three times in an identical or different manner by halogen,cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy having 1 to 5 identicalor different halogen atoms, such as fluorine and chlorine atoms.

Y preferably represents C₁ -C₆ -alkylene, C₁ -C₆ -hydroxyalkylene, C₁-C₄ -alkoxy-C₁ -C₆ -alkylene, C₁ -C₄ -alkylcarbonyloxy-C₁ -C₆ -alkylene,cyano-C₁ -C₆ -alkylene or C₁ -C₄ -halogenoalkylene having 1 to 5identical or different halogen atoms, such as fluorine and chlorineatoms; or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkylene, C₂ -C₄ -alkenylene or C₁-C₄ -alkenyloxy which are optionally substituted once to three times inan identical or different manner by fluorine, chlorine or methyl.

R¹ particularly preferably represents methyl, ethyl, n- or i-propyl orn-, i-, s- or t-butyl; CH₂ F, CHF₂, CF₃, CH₂ Cl, CH₂ Br or CHClCH₃ ;methoxy, ethoxy, methoxymethyl or ethoxymethyl; methylthiomethyl orcyclopropyl.

R² particularly preferably represents hydrogen, chlorine, bromine,cyano, nitro or thiocyanato; methoxycarbonyl, ethoxycarbonyl,i-propoxycarbonyl or n-propoxycarbonyl; allyloxycarbonyl; SCF₃, SCCl₂ F,SOCF₃, SOCCl₂ F, SO₂ CF₃, SO₂ CCl₂ F, SCHF₂, SOCHF₂, SO₂ CHF₂ or CSNH₂.

R³ particularly preferably represents hydrogen, methyl, ethyl or n- ori-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl orn-butoxymethyl; methylcarbonyl or methylsulfonyl; phenylcarbonyl orbenzyl, in each case optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, methyl ortrifluoromethyl; or cyclopropyl.

R⁴ particularly preferably represents phenyl which is optionallysubstituted once to three times in an identical or different manner,possible substituents being halogen, nitro, cyano, C₁ -C₁₂ -alkyl, C₁-C₁₂ -halogenoalkyl having 1 to 5 identical or different halogen atoms,such as fluorine and chlorine atoms, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy having 1 to 5 identical or different halogen atoms, suchas fluorine and chlorine atoms, C₁ -C₄ -alkylthio, C₁ -C₄-halogenoalkylthio having 1 to 5 identical or different halogen atoms,such as fluorine and chlorine atoms, C₂ -C₄ -alkenyl, C₂ -C₄-halogenoalkenyl having 1 to 5 identical or different halogen atoms,such as fluorine and chlorine atoms, and phenoxy, phenylthio orbenzyloxy, in each case optionally substituted once to three times in anidentical or different manner by halogen, nitro, cyano, C₁ -C₄ -alkyl,C₁ -C₄ -halogenoalkyl having 1 to 5 identical or different halogenatoms, such as fluorine and chlorine atoms, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy having 1 to 5 identical or different halogen atoms, suchas fluorine and chlorine atoms, C₁ -C₄ -alkylthio, C₁ -C₄-halogenoalkylthio having 1 to 5 identical or different halogen atoms,such as fluorine or chlorine atoms, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, C₁-C₄ -alkylsulfonyl, C₁ -C₄ -halogenoalkylsulfonyl having 1 to 5identical or different halogen atoms, such as fluorine or chlorineatoms, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxy-carbonyl, thioamide, C₁-C₄ -alkoximino-C₁ -C₂ -alkyl or optionally C₁ -C₂ -alkyl-substituted1,2,4-oxdiazol-3-yl.

Y particularly preferably represents one of the groups

--CH₂ --, --CH(CH₃)--, --CH(C₂ H₅)--, --CH(n-C₃ H₇)--, --CH(i-C₃ H₇)--,--CH₂ CH₂ --, --CH(OH)--, --CH(OCH₃)--, --CH(O--CO--CH₃)--, --CH(CN)--,--CHF--, --CHCl--, ##STR6## --CH═CH-- or --CH₂ O--. R¹ especiallypreferably represents methyl, ethyl, n- or i-propyl or n-, i-, s- ort-butyl; CH₂ F, CHF₂, CF₃, CH₂ Cl, CH₂ Br, methoxy or ethoxy.

R² especially preferably represents hydrogen, chlorine, bromine, cyano,nitro, thiocyanato, methoxycarbonyl, ethoxycarbonyl, SCF₃, SOCF₃ or SO₂CF₃.

R³ especially preferably represents hydrogen, methyl, ethyl,methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl ormethylsulfonyl.

R⁴ especially preferably represents phenyl which is optionallysubstituted once to three times in an identical or different manner,possible substituents being fluorine, chlorine, bromine, nitro, cyano,methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl; methoxy, ethoxy,n- or i-propoxy or n-, i-, s- or t-butoxy; methylthio, CF₃, OCF₃, OCHF₂,SCF₃ or SCCl₂ F; CH₂ Br or CH₂ Cl, and phenoxy or benzyloxy which areoptionally substituted once to three times in an identical or differentmanner by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, methylthiomethyl, CF₃, OCF₃, OCHF₂,SCF₃, SCCl₂ F, CH₂ Br, CH₂ Cl, acetyl, ethylcarbonyl, methoxycarbonyl,methylsulfonyl, trifluoromethylsulfonyl, thioamide, methoximinomethyl,1-(methoximino)ethyl, 1-(ethoximino)ethyl, 1,2,4-oxdiazol-3-yl or5-methyl-1,2,4-oxdiazol-3-yl.

Y especially preferably represents --CH₂ --, --CH(CH₃)-- or --CH₂ O--,in particular --CH₂ -- or --CH(CH₃)--.

Preferred compounds according to the invention are substances of theformulae (IA) or (IB): ##STR7## in which R¹, R² and R³ represent theabove-mentioned general, preferred, particularly preferred andespecially preferred meanings and

X¹, X², X³, X⁴ and X⁵ represent the substituents mentioned above, underR⁴, generally, preferably, particularly preferably and especiallypreferably for the phenyl or phenoxy radical and

X¹, X², X³ and X⁴ in each case can also represent hydrogen.

Another preferred group of compounds are those of the formulae (IA) or(IB) in which the phenoxy radical is in the para-position relative tothe NR³ --CO--CH₂ -- or NR³ --COCH(CH₃)-- group, among these compounds,those in which the substituents X¹, X², X³ and X⁴ represent hydrogenbeing particularly preferred.

Another preferred group of compounds are those in which R¹ representsalkoxyalkyl, alkylthioalkyl, alkylthio or optionally substitutedcycloalkyl.

Another preferred group of compounds are those in which R³ representsalkylsulfonyl or in each case optionally substituted arylcarbonyl,arylsulfonyl or cycloalkyl.

Another preferred group of compounds are those in which R⁴ representsphenyl which is substituted by benzyloxy optionally substituted asdescribed above, the benzyloxy radical preferably being in thepara-position relative to the substituent already present on the phenylring.

Another group of preferred compounds are those in which R² representscyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl,alkylthio, halogenoalkylthio, alkylsulfinyl, halogenoalkylsulfinyl,alkylsulfonyl, halogenoalkylsulfonyl or thiocarbamoyl, in particularcyano.

Another group of preferred compounds are those of the formulae (IA) or(IB) in which X⁵ represents alkylthio, halogenoalkylthio,alkylthioalkyl, alkylsulfonyl, halogenoalkylsulfonyl, alkoxycarbonyl,thioamide, alkoximinoalkyl or optionally alkyl-substituted oxdiazolyl,wherein the particular number of carbon atoms is mentioned above underR⁴ and X¹, X², X³ and X⁴ in particular represent hydrogen.

The above-mentioned general definitions of radicals and explanations arethose given in preferred ranges apply accordingly to the end product andto the starting substances and intermediates. These definitions ofradicals can be combined with one another as desired, that is to sayalso between the particular preferred ranges.

Compounds of the formula (I) which are preferred according to theinvention are those in which a combination of the meanings listed aboveas preferred (preferably) is present.

Compounds of the formula (I) which are particularly preferred accordingto the invention are those in which a combination of the meanings listedabove as particularly preferred is present.

Compounds of the formula (I) which are especially preferred according tothe invention are those in which a combination of the meanings listedabove are especially preferred if present.

In the definitions of radicals listed above and below, hydrocarbonradicals, such as alkyl or alkenyl--including in combination withheteroatoms, such as alkoxy or alkylthio--are, where possible, in eachcase straight-chain or branched.

In addition to the Preparation Examples, the following compounds of theformula (IC) may be mentioned specifically:

                  TABLE A                                                         ______________________________________                                                                      (IC)                                            1 #STR8##                                                                     R.sup.1 R.sup.2  R.sup.3    Y      X                                          ______________________________________                                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-SCH.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-CO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-CN                                       C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-Cl                                       C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-SCH.sub.3                                C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-SO.sub.2 CF.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CHCH.sub.3                                                                           4-CO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2 CH.sub.2                                                                    4-CN                                       C.sub.2 H.sub.5                                                                       Cl       H          CHCH   4-CN                                       C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2 O                                                                           4-CN                                       C.sub.2 H.sub.5                                                                       Cl       CH.sub.3   CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       Cl       CH.sub.3   CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       Cl       CH.sub.3   CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       Cl       COCH.sub.3 CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-SCH.sub.3                                C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2                                                                             4-CO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Br       H          CHCH.sub.3                                                                           4-CN                                       C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2 CH.sub.2                                                                    4-CN                                       C.sub.2 H.sub.5                                                                       Br       H          CHCH   4-CN                                       C.sub.2 H.sub.5                                                                       Br       H          CH.sub.2 O                                                                           4-CN                                       C.sub.2 H.sub.5                                                                       Br       CH.sub.3   CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       Br       CH.sub.3   CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       Br       CH.sub.3   CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       Br       CH.sub.3   CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       Br       COCH.sub.3 CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-SCH.sub.3                                C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       NO.sub.2 H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-CN                                       CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-NO.sub.2                                 CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-Cl                                       CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-OCF.sub.3                                CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-CF.sub.3                                 CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-SCF.sub.3                                CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-SCH.sub.3                                CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-CO.sub.2 CH.sub.3                        CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2 CH.sub.2                                                                    4-CN                                       C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-NO.sub.2                                 CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CHCH   4-CN                                       CH.sub.3                                                                              CO.sub.2 Et                                                                            H          CH.sub.2 O                                                                           4-CN                                       CH.sub.3                                                                              CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-CN                                       CH.sub.3                                                                              CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-NO.sub.2                                 CH.sub.3                                                                              CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-Cl                                       CH.sub.3                                                                              CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-OCF.sub.3                                CH.sub.3                                                                              CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       CO.sub.2 Me                                                                            H          CH.sub.2                                                                             4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2                                                                             4-CO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2 CH.sub.2                                                                    4-CN                                       C.sub.2 H.sub.5                                                                       CN       H          CHCH   4-CN                                       C.sub.2 H.sub.5                                                                       CN       H          CH.sub.2 O                                                                           4-CN                                       C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-CN                                       C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-Cl                                       C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-OCF.sub.3                                C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-CF.sub.3                                 C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-SCF.sub.3                                C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-SCH.sub.3                                C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        C.sub.2 H.sub.5                                                                       Cl       H          CH.sub.2                                                                             4-NO.sub.2                                 C.sub.2 H.sub.5                                                                       CSNH.sub.2                                                                             H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-CN                                       CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-NO.sub.2                                 CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-Cl                                       CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-OCF.sub.3                                CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-CF.sub.3                                 CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-SCF.sub.3                                CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-SCH.sub.3                                CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-SO.sub.2 CH.sub.3                        CH.sub.3                                                                              SCN      H          CH.sub.2                                                                             4-SO.sub.2 CF.sub.3                        OC.sub.2 H.sub.5                                                                      CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-CN                                       OC.sub.2 H.sub.5                                                                      CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-NO.sub.2                                 OC.sub.2 H.sub.5                                                                      CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-Cl                                       OC.sub.2 H.sub.5                                                                      CO.sub.2 Et                                                                            H          CH.sub.2                                                                             4-OCF.sub.3                                ______________________________________                                    

If, for example, 5-amino-3-methyl-isothiazole and[4-(4-cyano)phenoxy]phenylacetyl chloride are used as startingsubstances in the preparation of compounds of the formula (I) accordingto process (a), the course of the reaction can be represented by thefollowing equation: ##STR9##

If, for example,5-[4-(4-cyano)phenoxy]-phenylacetylamino-3-methyl-isothiazole andbromine are used as starting substances in the preparation of compoundsof the formula (I) according to process (b/α), the course of thereaction can be represented by the following equation: ##STR10##

If, for example,5-[4-(4-cyano)phenoxy]-phenylacetylamino-3-methyl-isothiazole and nitricacid, if appropriate in the presence of acetic acid, are used as thestarting substances in the preparation of compounds of the formula (I)according to process (b/β), the course of the reaction can berepresented by the following equation: ##STR11##

If, for example, β-amino-α-ethoxy-carbonyl-thiocrotonic acid[4-(4-cyano)phenoxyphenylacetyl]amide is used as the starting substanceand H₂ O₂ is used as the oxidizing agent in the preparation of compoundsof the formula (I) according to process (c), the course of the reactioncan be represented by the following equation: ##STR12##

The 5-aminoisothiazoles of the formula (II) to be used as startingsubstances in process (a) according to the invention are known (cf., forexample, DE-A 4 328 425, DE-A 2 249 162, WO-A 93/19 054, WO-A 94/21 617or J. Het. Chem. 1989, 26, 1575) and/or can be prepared by known methods(cf., for example, the above-mentioned literature references).

The acid halides of the formula (III) furthermore to be used as startingsubstances in process (a) according to the invention are generally knowncompounds of organic chemistry. In the formula (III), Hal preferablyrepresents chlorine or bromine.

Formula (IV) provides a general definition of theβ-amino-thiocrotonamides to be used as starting substances in process(c) according to the invention. In this formula, R¹, R⁴ and Ypreferably, particularly preferably and especially preferably representthose meanings which have already been mentioned above as preferred,particularly preferred and especially preferred for R¹, R⁴ and Y inconnection with the description of the compounds of the formula (I)according to the invention. R²⁻¹ preferably represents cyano or C₁ -C₄-alkoxycarbonyl, particularly preferably cyano, methoxycarbonyl,ethoxycarbonyl, i-propoxycarbonyl or n-propoxycarbonyl, and especiallypreferably cyano, methoxycarbonyl or ethoxycarbonyl.

The β-amino-thiocrotonamides of the formula (IV) are novel. However,they can be obtained in a generally known manner, by a process in whichacid halides of the formula (III) are reacted with thiocyanates of theformula (V)

    M--SCN                                                     (V)

in which

M represents an alkali metal, preferably potassium or sodium,

if appropriate in the presence of a diluent, for example a halogenatedaliphatic or aromatic hydrocarbon or an ether, nitrile or amide, attemperatures between -40° C. and +120° C., preferably between 0° C. and80° C.,

and the compounds formed in this reaction, of the formula (VI)

    R.sup.4 --Y--CO--NCS                                       (VI)

in which

R⁴ and Y have the above-mentioned meaning, are reacted, preferablydirectly without isolation, with compounds of the formula (VII)##STR13## in which R¹ and R²⁻¹ have the above-mentioned meaning,

if appropriate in the presence of a diluent, for example a halogenatedaliphatic or aromatic hydrocarbon or an ether, nitrile or amide, attemperatures between -40° C. and 120° C., preferably between 0° C. and80° C. (cf. also the general process instructions in J. Org. Chem. 1977,20, 3230 and Chem. Ber. 1961, 94, 2950).

The thiocyanates of the formula (V) and the compounds of the formula(VII) are generally known compounds of organic chemistry.

The process (a) described above for preparation of the compounds of theformula (I) is carried out in the presence of a diluent. All thecustomary solvents can be employed as diluents.

Diluents which can preferably be used are optionally halogenatedaliphatic or aromatic hydrocarbons, ethers or nitrites, such as, forexample, cyclohexane, toluene, chlorobenzene, chloroform, methylenechloride, dichloroethane, dioxane, tetrahydrofuran, diethyl ether oracetonitrile.

The process (a) described above for preparation of the compounds of theformula (I) is carried out in the presence of a base.

Bases which can be employed in process (a) are all the customary protonacceptors. Bases which can preferably be used are alkali metal oralkaline earth metal hydroxides, alkali metal or alkaline earth metalcarbonates or bicarbonates or nitrogen bases. Examples which may bementioned are sodium hydroxide, calcium hydroxide, potassium carbonate,sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine,pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene(DBN) and diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range inthe process (a) described. The reaction is in general carried out attemperatures between -40° C. and +200° C., preferably between 0° C. and100° C.

In carrying out the process (a) described above for preparation of thecompounds of the formula (I), in general 1 to 2 mol, preferably 1 to 1.5mol, of acid halide of the formula (III) are employed per mole of5-aminoisothiazole of the formula (II).

In some cases, it has proved advantageous here to employ the5-aminoisothiazoles of the formula (II) in the form of theirhydrohalides, such as, in particular, as hydrochlorides.

Working up and isolation of the end products are carried out in thegenerally known manner.

The process (b/α) described above for preparation of the compounds ofthe formula (I) is carried out by means of a halogenating agent.

All the customary halogenating agents can be employed for this process.Halogenating agents which can preferably be used are Cl₂, Br₂, hydrogenhalide acids or salts thereof, such as, for example, sodium hypochloriteand -bromite or potassium hypochlorite and -bromite, SO₂ Cl₂, S₂ Cl₂,PCl₅ or N-bromosuccinimide.

If appropriate, the process (b/α) described above for preparation of thecompounds of the formula (I) is carried out in the presence of adiluent. Diluents which can preferably be used are optionallyhalogenated aliphatic or aromatic hydrocarbons, ethers, nitriles oramides, such as, for example, cyclohexane, toluene, chlorobenzene,chloroform, methylene chloride, dichloroethane, dioxane,tetrahydrofuran, diethyl ether, acetonitrile or dimethylformamide.

If appropriate, the process (b/α) described above for preparation of thecompounds of the formula (I) is carried out in the presence of acatalyst. Catalysts which can be employed are all the acid or basiccatalysts customary for a halogenation, such as, for example, hydrogenhalides or sodium acetate, and furthermore free radical initiators, suchas azoisobutyronitrile or dibenzoyl peroxide.

The reaction temperatures can be varied within a substantial range inthe process (b/α) described above. The reaction is in general carriedout at temperatures between -40° C. and 120° C., preferably between 0°C. and 80° C.

In carrying out the process (b/α) described above for preparation of thecompounds of the formula (I), in general 1 to 2 mol, preferably 1 to 1.5mol, of halogenating agent are employed per mole of acylated5-aminoisothiazole of the formula (Ia).

Working up and isolation of the end products are carried out in thegenerally known manner.

The process (b/β) described above for preparation of the compounds ofthe formula (I) is carried out by means of a nitrating reagent. All thecustomary nitrating reagents can be employed for this process. Nitratingreagents which can preferably be used are nitric acid, if appropriate insulfuric acid, water, acetic acid or acetic anhydride, N₂ O₅ in carbontetrachloride, methyl nitrate with BF₃, sodium nitrite intrifluoroacetic acid or N₂ O₄.

If appropriate, the process (b/β) described above for preparation of thecompounds of the formula (I) is carried out in the presence of adiluent. Diluents which can preferably be used are optionallyhalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride or chlorobenzene, or nitrobenzene.

The reaction temperatures can be varied within a substantial range inthe process (b/β) described above. The reaction is in general carriedout at temperatures between 0° C. and 100° C., preferably between 0° C.and 40° C.

In carrying out the process (b/β) described above for preparation of thecompounds of the formula (I), in general 1 to 5 mol, preferably 1 to 2mol, of nitrating reagent are employed per mole of acylated5-aminoisothiazole of the formula (Ia).

Working up and isolation of the end products are carried out in thegenerally known manner.

The process (c) described above for preparation of certain compounds ofthe formula (I) is carried out by means of an oxidizing agent.

Customary oxidizing agents can be employed for this process. Oxidizingagents which can preferably be used are iodine, bromine, chlorine orhydrogen peroxide (in this context, cf. also J. Org. Chem. 1977, 20,3230 and Chem. Ber. 1961, 94, 2950).

If appropriate, the process (c) described above for preparation ofcertain compounds of the formula (I) is carried out in the presence of adiluent. Diluents which can preferably be used are optionallyhalogenated aliphatic or aromatic hydrocarbons, ethers, nitriles oramides, such as, for example, cyclohexane, toluene, chlorobenzene,chloroform, methylene chloride, dichloroethane, dioxane,tetrahydrofuran, diethyl ether, acetonitrile or dimethylformamide.

The reaction temperatures can be varied within a substantial range inthe process (c) described above. The reaction is in general carried outat temperatures between -40° C. and 120° C., preferably between 0° C.and 80° C.

Working up and isolation of the end products are carried out in thegenerally known manner.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene field, and have good plant tolerance andfavorable toxicity to warm-blooded animals. They may be preferablyemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The above-mentioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus Spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Spodoptera litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp. and Trichodorus spp.

The compounds of the formula (I) according to the invention aredistinguished in particular by a high insecticidal and acaricidalactivity.

They can be employed particularly successfully for controllingphytopathogenic insects, such as, for example, against the larvae of themustard beetle (Phaedon cochlaeriae), caterpillars of the cabbage moth(Plutella maculipennis), the green rice cicada (Nephotettix cincticeps)and caterpillars of the owlet moth (Spodoptera frugiperda), or forcontrolling phytopathogenic mites, such as, for example, against thecommon spider mite (Tetranychus urticae).

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents, and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulfoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulfite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms, inter alia.

Particularly favorable mixing partners are, for example, the following:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazol-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinolin sulfate, methyl(E)-2-{2-[6-(2-cyano-phenoxy)-pyrimidine-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate.

calcium polysulfide, captafol, captan, carbendazim, carboxin,chinomethionate (quinomethionate), chloroneb, chloropicrin,chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole,cyprofuram,

dichlorophen, diclobutrazole, diclofluanid, diclomezin, dichloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithione, ditalimfos, dithianone, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadin, iprobenfos (IBP), iprodione,isoprothiolan,

kasugamycin, copper formulations, such as: copper hydroxide, coppernaphthenate, copper oxychloride, copper sulfate, copper oxide,oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax,myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, penycuron, phosdiphen, phthalide, pimaricin,piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon,propamocarb, propiconazole, propineb, pyrazophos, pyrifenox,pyrimethanil, pyroquilon,

quintozene (PCNB),

sulfur and sulfur formulations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolcophos-methyl, tolylfluanide,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforin, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinon, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulfate and other copperformulations.

Insecticides/Acaracides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184 699, cloethocarb, clorethoxyfos, chlordenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezin, cyanophos, cycloprothrin,cyflurthrin, cyhalotrin, cyhexatin, cypermethrin, cyromazin,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

ediphenphos, emamectin, esfenvalerate, ethiofencarb, ethion,ethofenprox, ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin, lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon, M, oxydeprofos,

parathion A, parathion A, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorovinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active compounds, such as herbicides or withfertilizers and growth regulators, is also possible.

The active compounds according to the invention can furthermore bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with synergisticagents. Synergistic agents are compounds which increase the action ofthe active compounds, without it being necessary for the synergisticagent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompounds are distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The active compounds according to the invention act not only againstplant, hygiene and stored products pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasite include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otabiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

For example, they show an outstanding activity against Boophilusmicroplus and Lucilia cuprina.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boli, the feed-through process and suppositories, by parenteraladministration, such as, for example, by injection (intramuscular,subcutaneous, intravenous, intraperitoneal and the like), implants, bynasal administration, by dermal use in the form, for example, of dippingor bathing, spraying, pouring on and spotting on, washing and powdering,and also with the aid of molded articles containing the active compound,such as collars, ear marks, tail marks, limb bands, halters, markingdevices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10,000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention also have a potent insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred--butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis,Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis,Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as

Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood paneling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater-repellent, if appropriate siccative and UW stabilizers and ifappropriate dyestuffs and pigments, as well as other processingauxiliaries.

The insecticidal compositions or concentrates used for preservation ofwood and derived timber products comprise the active compound accordingto the invention in a concentration of 0.0001 to 95% by weight, inparticular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Such water-insoluble, oily and oil-likesolvents of low volatility which are used as corresponding mineral oilsor aromatic fractions thereof or solvent mixtures containing mineraloils, preferably test benzine, petroleum and/or alkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., test benzinehaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashopoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, providing that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repellent agents, smell correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyl resin or modified alkyl resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulfonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether, or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the above-mentioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present Application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron,

and fungicides, such as epoxyconazole, hexaconazole, azaconazole,propioconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolyfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3 -one.

The preparation and the use of the active compounds according to theinvention can be seen from the following Examples.

PREPARATION EXAMPLES Example 1 ##STR14## (Process a)

A solution of 5.43 g (0.02 mol) of [4-(4-cyano)phenoxy]-phenylacetylchloride in 20 ml of acetonitrile is added dropwise to a solution of3.01 g (0.02 mol) of 5-amino-3-methyl-isothiazole hydrochloride and 3.32g (0.042 mol) of pyridine in 100 ml of acetonitrile. The mixture isstirred at 25° C. for 18 hours and then concentrated to dryness. Thereaction mixture is taken up in water/ethyl acetate and the organicphase is washed several times with 10% strength sodium hydroxidesolution. After drying and concentration, a viscous residue is obtained,which is purified by chromatography over silica gel with ethyl acetateas the mobile phase.

2.20 g (31% of theory) of5-[4-(4-cyano)phenoxy]phenylacetylamino-3-methylisothiazole areobtained.

¹ H NMR (d₆ -DMSO): δ=1.18, 2.31, 3.81, 4.04, 6.74, 7.1-7.2, 7.40, 7.82ppm

Example 2 ##STR15## (Process b/α)

0.22 g (0.00134 mol) of bromine in 1 ml of methylene chloride is addeddropwise to a solution of 0.40 g (0.00112 mol) of5-[4-(4-cyano)phenoxy]phenylacetylamino-3-methylisothiazole (Example 1)in 10 ml of methylene chloride at 5° C. and the mixture is stirred at25° C. for 18 hours. After the solvent has been removed in vacuo, 0.50 g(92% of theory) of4-bromo-5-[4-cyano)phenoxy]phenylacetamino-3-methylisothiazole ofmelting point 197-198° C. is obtained.

The following compounds of the formula (I) are obtained analogously orin accordance with the general instructions on the preparation:

                                      TABLE 1                                     __________________________________________________________________________                                                   (I)                            1 #STR16##                                                                                                              Physical data                                                                 (.sup.1 H NMR; ppm,                 Ex.                                       in d.sub.6 -DMSO) or                No.                                                                              R.sup.1                                                                           R.sup.2                                                                          R.sup.3                                                                          Y   R.sup.4                  melting point (°             __________________________________________________________________________                                              C.))                                4  CH.sub.3                                                                          H  H  CH.sub.2                                                                          2 #STR17##               2.31; 3.77; 6.73; 7.00;                                                       7.3-7.5; 12.05                      5  CH.sub.3                                                                          H  H  CH.sub.2                                                                          3 #STR18##               2.31; 3.78; 6.73; 7.0- 7.1;                                                   7.3-7.4; 12.06                      6  CH.sub.3                                                                          H  H  CH.sub.2                                                                          4 #STR19##               137-138                             7                                                                             8                                                                             9  CH.sub.3                                                                          Br H  CH.sub.2                                                                          3 #STR20##               189-190                             10 CH.sub.3                                                                          H  H  CH.sub.2                                                                          5 #STR21##               2.31; 2.73; 3.80; 6.74;                                                       7.0-7.2; 7.38; 7.70; 12.1           11 CH.sub.3                                                                          Br H  CH.sub.2                                                                          4 #STR22##               2.31; 2.46; 3.75; 7.0-7.1;                                                    7.3-7.4; 7.6-7.7; 12.04             12 CH.sub.3                                                                          Br H  CH.sub.2                                                                          5 #STR23##               2.45; 2.77; 3.94; 7.0-7.1;                                                    7.3-7.4; 7.6-7.7; 8.98*             13 CH.sub.3                                                                          H  H  CH.sub.2                                                                          6 #STR24##               2.32; 3.83; 6.74; 7.1-7.2;                                                    7.4-7.5; 8.2-8.3; 12.09             14 CH.sub.3                                                                          Br H  CH.sub.2                                                                          6 #STR25##               2.37; 4.03; 7.0-7.1; 7.4-7.5;                                                 8.2-8.3; 11.59                      15                                                                            16 C.sub.2 H.sub.5                                                                   CN H  CH.sub.2                                                                          7 #STR26##               1.35; 2.86; 3.94; 6.9-7.5;                                                    9.62*                               17 C.sub.2 H.sub.5                                                                   CN H  CH.sub.2                                                                          3 #STR27##               1.24; 2.80; 3.97; 4.9-7.4;                                                    12.85                               18 C.sub.2 H.sub.5                                                                   CN H  CH.sub.2                                                                          4 #STR28##               1.31; 2.46; 2.84; 3.88;                                                       6.9-7.1; 7.3; 9.21*                 19 C.sub.2 H.sub.5                                                                   CN H  CH.sub.2                                                                          6 #STR29##               1.24; 2.80; 4.03; 7.0-7.1;                                                    7.20; 8.24; 12.88*                  20 CH.sub.3                                                                          CN H  CH.sub.2                                                                          7 #STR30##               2.53; 3.94; 6.9-7.1; 7.2-7.7*       21 C.sub.4 H.sub.9 -t                                                                H  H  CH.sub.2                                                                          7 #STR31##               1.30; 3.82; 6.67- 7.10; 7.35;                                                 7.60; 8.74                          22 C.sub.4 H.sub.9 -t                                                                Cl H  CH.sub.2                                                                          7 #STR32##               1.41; 3.90; 6.99; 7.38; 7.61;                                                 8,30*                               23 CH.sub.3                                                                          CN H  CH.sub.2                                                                          8 #STR33##               2.50; 3.99; 6.9- 7.1; 7.35;                                                   7.70                                24 CH.sub.3                                                                          CN H  CH.sub.2                                                                          2 #STR34##               2.50; 3.57; 7.03; 7.3-7.5           25 CH.sub.3                                                                          CN H  CH.sub.2                                                                          4 #STR35##               2.24; 2.43; 3.96; 6.99; 7.30        26 C.sub.2 H.sub.5                                                                   H  H  CH.sub.2                                                                          7 #STR36##               1.26; 2.74; 3.83- 5.48; 7.05;                                                 7.27; 7.64*                         27 CH.sub.3                                                                          H  H  CH.sub.2                                                                          8 #STR37##               2.50; 3.80; 6.74; 7.09; 7.38;                                                 7.72                                28 CH.sub.3                                                                          H  H  CH.sub.2 O                                                                        7 #STR38##               175-76                              29 CH.sub.3                                                                          H  H  CH.sub.2                                                                          9 #STR39##               198-99                              30 CH.sub.3                                                                          Cl H  CH.sub.2 O                                                                        7 #STR40##               175-76                              31 CH.sub.3                                                                          Cl H  CH.sub.2                                                                          9 #STR41##               2.38; 3.82; 5.07; 6.90,                                                       7.2-7.4*                            32 CH.sub.3                                                                          Br H  CH.sub.2                                                                          9 #STR42##               2.41; 3.82; 5.07; 7.03;                                                       7.2-7.4*                            33 CH.sub.3                                                                          H  H  CH.sub.2                                                                          0 #STR43##               154-55                              34 CH.sub.3                                                                          H  H  CH.sub.2                                                                          1 #STR44##               184                                 35 CH.sub.3                                                                          Cl H  CH.sub.2                                                                          8 #STR45##               59-60                               36 CH.sub.3                                                                          Br H  CH.sub.2                                                                          8 #STR46##               60-62                               37 CH.sub.3                                                                          Cl H  CH.sub.2                                                                          0 #STR47##               178-79                              38 CH.sub.3                                                                          Br H  CH.sub.2                                                                          0 #STR48##               171                                 39 CH.sub.3                                                                          Br H  CH.sub.2                                                                          1 #STR49##               168-70                              40 CH.sub.3                                                                          Cl H  CH.sub.2                                                                          1 #STR50##               211-12                              41 CH.sub.3                                                                          Br H  CH.sub.2                                                                          2 #STR51##               2.43; 2.74; 3.89; 7.15; 7.36;                                                 7.65*                               42 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          5 #STR52##               185                                 43 C.sub.2 H.sub.5                                                                   Br H  CH.sub.2                                                                          5 #STR53##               196-97                              44 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          4 #STR54##               1.24; 2.49; 2.73; 3.85; 6.98;                                                 7.28*                               45 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          2 #STR55##               90-92                               46 CH.sub.3                                                                          CN H  CH.sub.2                                                                          3 #STR56##               198                                 47 C.sub.2 H.sub.5                                                                   Br H  CH.sub.2                                                                          3 #STR57##               128                                 48 CH.sub.3                                                                          Br H  CH.sub.2                                                                          3 #STR58##               148-49                              49 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          3 #STR59##               1.28; 2.59; 2.68; 3.89; 7.01;                                                 7.36; 7.94; 8.21*                   50 CH.sub.3                                                                          CN H  CH.sub.2                                                                          4 #STR60##               202-03                              51 CH.sub.3                                                                          Br H  CH.sub.2                                                                          4 #STR61##               124-25                              52 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          4 #STR62##               1.28; 2.23; 3.87; 4.00; 6.98;                                                 7.01; 7.32; 7.63; 8.13*             53 C.sub.2 H.sub.5                                                                   Br H  CH.sub.2                                                                          4 #STR63##               1.28; 2.22; 3.86; 4.00; 6.99;                                                 7.02; 7.31; 7.62; 8.12*             54 C.sub.2 H.sub.5                                                                   CI H  CH.sub.2                                                                          5 #STR64##               1.26; 2.71; 3.89; 6.98; 7.01;                                                 7.35; 7.89*                         55 C.sub.2 H.sub.5                                                                   H  H  CH.sub.2                                                                          6 #STR65##               160-61                              56 C.sub.2 H.sub.5                                                                   Cl H  CH.sub.2                                                                          6 #STR66##               1.29; 2.74; 3.89; 7.12; 7.36;                                                 8.09; 8.12; 8.73*                   __________________________________________________________________________     *in CDCl.sub.3 -                                                         

USE EXAMPLES Example A

Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae Phaedon cochleariae, as long as theleaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the beetle larvae has been killed; 0% means that none of thebeetle larvae has been killed.

In this test, for example, the compounds of Preparation Examples 1, 19,20, 22, 23, 29, 31, 32, 33, 37, 40, 43, 44, 46, 49, 50, 51, 54 and 55caused a destruction of 100% after 7 days at an active compoundconcentration of, for example, 0.1%.

Example B

Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compond, 1 part by weight ofactive compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the diamond-back moth Plutellamaculipennis while the leaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the caterpillars has been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the compounds of the Preparation Examples 1and 19 caused a destruction of 100% after 7 days at an active compoundconcentration of, for example, 0.1%.

Example C

Spodoptera Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the owlet moth Spodoptera frugiperda, aslong as the leaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the caterpillars has been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the compounds of Preparation Examples 1, 19,20, 23, 34, 25, 27, 28, 30, 35, 36, 37, 42, 44, 49 and 55 caused adestruction of 100% after 7 days at an active compound concentration of,for example, 0.1%.

Example D

Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with larvae of the green rice cicada Nephotettix cincticeps, aslong as the seedlings are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the cicadas have been killed; 0% means that none of the cicadashas been killed.

In this test, for example, the compounds of Preparation Examples 19, 20,26, 27, 35, 41, 42, 48 and 51 caused a destruction of 100% after 6 daysat an active compound concentration of, for example, 0.1%.

Example E

Tetranychus Test (OP-Resistant/Dipping Treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentrations.

Bean plants (Phaseolus vulgaris) heavily infested by all developmentstages of the common spider mite Tetranychus urticae are dipped in anactive compound preparation of the desired concentration.

After the desired time, the action in % is determined. 100% means thatall the spider mites have been killed; 0% means that none of the spidermites has been killed.

In this test, for example, the compound of Preparation Example 1 causeda destruction of 100% after 13 days at an active compound concentrationof, for example, 0.01%.

Example F

Myzus Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested with thepeach aphid (Myzus persicae) are treated by being dipped into thepreparation of the active compound of the desired concentration.

After the desired time, the destruction in % is determined. 100% meansthat all the aphids have been killed; 0% means that none of the aphidshas been killed.

In this test, for example, the compounds according to PreparationExamples 25, 26, 31, 41 and 51 caused a destruction of at least 80%after 6 days at an active compound concentration of, for example, 0.1%.

Example G

Test with Boophilus microplus Resistant/SP-Resistant Parkhurst Strain

Test animals: Adult satiated females

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with seven parts by weight of the solvent/emulsifiermixture indicated above, and the emulsion concentrate thus obtained isdiluted with water to the particular desired concentration.

10 adult Boophilus microplus res. are immersed for 1 minute in theactive compound preparation to be tested. After transfer to plasticbeakers and storage in a controlled-environment chamber, the degree ofdestruction is determined.

100% here means that all the ticks have been killed; 0% means that noneof the ticks has been killed.

In this test, for example, the compounds according to PreparationExamples 1 and 2 cause a degree of destruction of 100% at an activecompound concentration of, for example, 20 μg/animal.

Example H

Test with Fly Larvae/Development-Inhibiting Action

Test animals: All larval stages of Lucilia cuprina (OP-resistant)

[Pupae and adults (without contact with the active compound)]

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with seven parts by weight of the above-mentionedsolvent/emulsifier mixture, and the emulsion concentrate thus obtainedis diluted with water to the particular desired concentration.

30-50 larvae per concentration are placed on horsemeat (1 cm³) in glasstubes, onto which 500 μl of the dilution to be tested are pipetted. Theglass tubes are placed in plastic beakers, the bases of which arecovered with marine sand, and kept in a controlled-environment chamber(26° C.±1.5° C., 70% relative humidity ±10%). The active compoundcontrol is carried out after 24 hours and 48 hours (larvicidal action).After the larvae have migrated (about 72 hours), the glass tubes areremoved and perforated plastic lids are placed on the beakers. After11/2 times the development period (hatching of the control flies), theflies which have hatched and the pupae/pupal shells are counted.

Criteria for the action are the onset of death in the treated larvaeafter 48 hours (larvicidal effect) or the inhibition of hatching of theadult from the pupae or the inhibition of pupation. Criteria for the invitro action of a substance are the inhibition of flea development or astop in development before the adult stage. 100% larvicidal action heremeans that all the larvae have died after 48 hours. 100%development-inhibiting action means that no adult flies have hatched.

In this test, for example, the compounds according to PreparationExamples 1 and 2 had an action of 100% at an active compoundconcentration of, for example, 1000 ppm.

Example I

Test with Cat Fleas/Development-Inhibiting Action

Test animals: All stages (eggs, larvae, pupi and adult) ofCtenocephalides felis

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with 7 parts by weight of the above-mentionedsolvent/emulsifier mixture, and the emulsion concentrate thus obtainedis diluted with water to the particular desired concentration.

200 μl of this active compound preparation are added to 1.8 g ofbreeding medium (blood meal medium: 125 parts of marine sand, 20 partsof rat food, 3 parts of blood meal, 2 parts of dried yeast) indisposable tubes of 2.0 cm diameter and the components are mixedhomogeneously and dried overnight. A spatula-tip of sieved flea eggs(from artificially infected cats) is then added.

The activity of the active compound preparation is determined every 2days, up to 11/2 times the development time of the control batch, byinvestigating the batches for development stages of the fleas.

Criteria for the in vitro action of a substance are the inhibition offlea development or a stop in development before the adult stage. 100%here means that no adult fleas developed; 0% means that adult fleashatched.

In this test, for example, the compound according to Preparation Example2 had an action of 100% at a concentration of, for example, 100 ppm.

Example K

Test with Flies (Musca domestica)

Test animals: Adult Musca domestica, Reichswald strain (OP-, SP-,carbamate-resistant)

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with 7 parts of the above-mentionedsolvent/emulsifier mixture, and the emulsion concentrate thus obtainedis diluted with water to give the particular desired concentration.

2 ml of this active compound preparation are pipetted onto disks offilter paper (diameter 9.5 cm) in Petri dishes of appropriate size.After the filter disks have dried, 25 test animals are transferred tothe Petri dishes and the dishes are covered.

The activity of the active compound preparation is determined after 1,3, 5 and 24 hours. 100% here means that all the flies have been killed;0% means that none of the flies has been killed.

In this test, for example, the compound according to Preparation Example2 had an action of 100% at an active compound concentration of, forexample, 1000 ppm.

Example L

Cockroach Test

Test animals: Periplaneta americana

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompounds are mixed with seven parts of the above-mentionedsolvent/emulsifier mixture, and the emulsion concentrate thus obtainedis diluted with water to the particular desired concentration.

2 ml of this active compound preparation are pipetted onto disks offilter paper (diameter 9.5 cm) in Petri dishes of appropriate size.After the filter disks have dried, 5 test animals P. americana aretransferred and the dishes are covered.

The activity of the active compound preparation is determined after 3days. 100% here means that all the cockroaches has been killed; 0% meansthat none of the cockroaches has been killed.

In this test, for example, the compound according to Preparation Example2 had an activity of 100% at an active compound concentration of, forexample, 1000 ppm.

We claim:
 1. Compounds of the formula (I) ##STR67## in which R¹represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy,alkylthio or optionally substituted cycloalkyl,R² represents hydrogen,halogen, nitro, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio,halogenoalkylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl,or halogenoalkylsulfonyl, R³ represents hydrogen, alkyl, halogenoalkyl,alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionallysubstituted arylcarbonyl, arylsulfonyl or arylalkyl or optionallysubstituted cycloalkyl, R⁴ represents optionally substituted aryl,optionally substituted cycloalkyl or optionally substituted cycloalkenyland Y represents optionally substituted alkylene, alkenylene oralkylenoxy.
 2. Compounds of the formula (I) according to claim 1, inwhichR¹ represents C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl having 1 to 5identical or different halogen atoms, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁-C₄ -alkylthio-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, orrepresents C₃ -C₆ -cycloalkyl which is optionally substituted once tothree times in an identical or different manner by C₁ -C₄ -alkyl orhalogen, R² represents hydrogen, halogen, nitro, C₁ -C₄-alkoxy-carbonyl, C₂ -C₄ -alkenyloxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄-halogenoalkylthio having 1 to 5 identical or different halogen atoms,C₁ -C₄ -alkylsulfinyl, C₁ -C₄ -halogenoalkylsulfinyl having 1 to 5identical or different halogen atoms, C₁ -C₄ -alkylsulfonyl or C₁ -C₄-halogenoalkylsulfinyl having 1 to 5 identical or different halogenatoms, R³ represents hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkylhaving 1 to 5 identical or different halogen atoms, C₁ -C₄ -alkoxy-C₁-C₄ -alkyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkylsulfonyl orphenylcarbonyl, phenylsulfonyl or benyl, in each case optionallysubstituted in the phenyl ring once to three times in an identical ordifferent manner, substituents in each case being halogen, nitro, cyano,C₁ -C₄ -alkyl, C₁ -C₂ -halogenoalkyl having 1 to 5 identical ordifferent halogen atoms, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂-halogenoalkoxy having 1 to 5 identical or different halogen atoms, orC₁ -C₂ -halogenoalkylthio having 1 to 5 identical or different halogenatoms, or represents C₃ -C₆ -cycloalkyl which is optionally substitutedonce to three times in an identical or different manner by C₁ -C₄ -alkylor halogen, R⁴ represents phenyl which is optionally substituted once tothree times in an identical or different manner, substituents beinghalogen, nitro, cyano, C₁ -C₁₂ -alkyl, C₁ -C₁₂ -halogenoalkyl having 1to 5 identical or different halogen atoms, C₁ -C₁₂ -alkoxy, C₁ -C₁₂-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C₁-C₁₂ -alkylthio, C₁ -C₁₂ -halogenoalkylthio having 1 to 5 identical ordifferent halogen atoms, C₂ -C₁₂ -alkenyl, C₂ -C₁₂ -halogenoalkenylhaving 1 to 5 identical or different halogen atoms, C₃ -C₈ -cycloalkylwhich is optionally substituted once to three times in an identical ordifferent manner by C₁ -C₄ -alkyl or halogen, and phenyl, phenoxy,phenylthio, benzyl or benzyloxy, in each case optionally substitutedonce to three times in an identical or different manner by halogen,nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl having 1 to 5identical or different halogen atoms, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C₁-C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio having 1 to 5 identical ordifferent halogen atoms, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, C₁ -C₄-alkylsulfonyl, C₁ -C₄ -halogenoalkylsulfonyl having 1 to 5 identical ordifferent halogen atoms, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxy-carbonyl, thioamide, C₁ -C₄ -alkoximino-C₁ -C₄ -alkyl oroptionally C₁ -C₄ -alkyl-substituted oxdiazolyl,or represents C₃ -C₈-cycloalkyl or C₅ -C₈ -cycloalkenyl, in each case optionally substitutedonce to three times in an identical or different manner, substituentsbeing C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl having 1 to 5 identical ordifferent halogen atoms, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy having 1to 5 identical or different halogen atoms, C₃ -C₈ -cycloalkyl and phenylwhich is optionally substituted once to three times in an identical ordifferent manner by halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄-halogenoalkyl having 1 to 5 identical or different halogen atoms, C₁-C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy having 1 to 5 identical ordifferent halogen atoms, and Y represents C₁ -C₆ -alkylene, C₁ -C₆-hydroxyalkylene, C₁ -C₄ -alkoxy-C₁ -C₆ -alkylene, C₁ -C₄-alkylcarbonyloxy-C₁ -C₆ -alkylene, cyano-C₁ -C₆ -alkylene or C₁ -C₄-halogenoalkylene having 1 to 5 identical or different halogen atoms, orC₃ -C₆ -cycloalkyl-C₁ -C₄ -alkylene, C₂ -C₄ -alkenylene or C₁ -C₄-alkenyloxy which are optionally substituted once to three times in anidentical or different manner by fluorine, chlorine or methyl. 3.Compounds of the formula (I) according to claim 1, in whichR¹ representsmethyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl; CH₂ F, CHF₂, CH₂Cl, CF₃, CH₂ Br, methoxy or ethoxy, R² represents hydrogen, chlorine,bromine, nitro, methoxycarbonyl, ethoxycarbonyl, SCF₃, SOCF₃ or SO₂ CF₃,R³ represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl,methylcarbonyl, phenylcarbonyl or methylsulfonyl, R⁴ represents phenylwhich is optionally substituted once to three times in an identical ordifferent manner, possible substituents being fluorine, chlorine,bromine, nitro, cyano, methyl, ethyl, n- or i-propyl or n-, i-, s- ort-butyl; methoxy, ethoxy, n- or i-propoxy or n, i-, s- or t-butoxy;methylthio, CF₃, OCF₃, OCHF₂, SCF₃ or SCCl₂ F; CH₂ Br or CH₂ Cl, andphenoxy or benzyloxy which are optionally substituted once to threetimes in an identical or different manner by fluorine, chlorine,bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, methylthiomethyl, CF₃, OCF₃, OCHF₂, SCF₃, SCCl₂ F, CH₂ Br,CH₂ Cl, acetyl, ethylcarbonyl, methoxycarbonyl, methylsulfonyl,trifluoromethylsulfonyl, thioamide, methoximinomethyl,1-(methoximino)ethyl, 1-(ethoximino)-ethyl, 1,2,4-oxdiazol-3-yl or5-methyl-1,2,4-oxdiazol-3-yl and Y represents --CH₂ --, --CH(CH₃)-- or--CH₂ O--.
 4. Compounds of the formula (I) according to claim 1, inwhichR¹ represents methyl, ethyl, n- or i-propyl or n-, i-, s- ort-butyl; CH₂ F, CHF₂, CF₃, CH₂ Cl, CH₂ Br or CHClCH₃ ; methoxy, ethoxy,methoxymethyl or ethoxymethyl; methylthiomethyl or cyclopropyl, R²represents hydrogen, chlorine, bromine, nitro, methoxycarbonyl,ethoxycarbonyl, i-propoxycarbonyl or n-propoxycarbonyl;allyloxycarbonyl; SCF₃, SCCl₂ F, SOCF₃, SOCCl₂ F, SO₂ CF₃, SO₂ CCl₂ F,SCHF₂, SOCHF₂, or SO₂ CHF₂, R³ represents hydrogen, methyl, ethyl or n-or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl orn-butoxymethyl; methylcarbonyl or methylsulfonyl; phenylcarbonyl orbenzyl, in each case optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, methyl ortrifluoromethyl; or cyclopropyl, R⁴ represents phenyl which isoptionally substituted once to three times in an identical or differentmanner, possible substituents being halogen, nitro, cyano, C₁ -C₁₂-alkyl, C₁ -C₁₂ -halogenoalkyl having 1 to 5 identical or differenthalogen atoms, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy having 1 to 5identical or different halogen atoms, C₁ -C₄ -alkylthio, C₁ -C₄-halogenoalkylthio having 1 to 5 identical or different halogen atoms,C₂ -C₄ -alkenyl, C₂ -C₄ -halogenoalkenyl having 1 to 5 identical ordifferent halogen atoms, and phenoxy, phenylthio or benzyloxy, in eachcase optionally substituted once to three times in an identical ordifferent manner by halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄-halogenoalkyl having 1 to 5 identical or different halogen atoms, C₁-C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy having 1 to 5 identical or differenthalogen atoms, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio having 1 to5 identical or different halogen atoms, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl,C₁ -C₄ -alkylsulfonyl, C₁ -C₄ -halogenoalkylsulfonyl having 1 to 5identical or different halogen atoms, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxy-carbonyl, thioamide, C₁ -C₄ -alkoximino-C₁ -C₂ -alkyl oroptionally C₁ -C₂ -alkyl-substituted 1,2,4-oxdiazol-3-yl and Yrepresents one of the groups--CH₂ --, --CH(CH₃)--, --CH(C₂ H₅)--,--CH(n-C₃ H₇)--, --CH(i-C₃ H₇)--, --CH₂ CH₂ --, --CH(OH)--,--CH(OCH₃)--, --CH(O--CO--CH₃)--, --CH(CN)--, --CHF--, --CHCl--,##STR68## --CH═CH-- or --CH₂ O--.
 5. A compound according to claim 2,wherein ifR¹ represents C₁ -C₄ -halogenoalkyl, the halogen atoms areselected from the group consisting of fluorine, chlorine and bromine; orR² represents C₁ -C₄ -halogenoalkylthio, the halogen atoms are selectedfrom the group consisting of fluorine and chlorine; or R² represents C₁-C₄ -halogenoalkylsulfonyl, the halogen atoms are selected from thegroup consisting of fluorine and chlorine; or R³ represents C₁ -C₄-halogenoalkyl, the halogen atoms are selected from the group consistingof fluorine and chlorine; or R³ represents C₁ -C₂ -halogenoalkyl, thehalogen atoms are selected from the group consisting of fluorine andchlorine; or R³ represents C₁ -C₂ -halogenoalkoxy, the halogen atoms areselected from the group consisting of fluorine and chlorine; or R³represents C₁ -C₂ -halogenoalkylthio the halogen atoms are selected fromthe group consisting of fluorine and chlorine; or R⁴ represents phenylsubstituted by C₁ -C₁₂ -halogenoalkyl, the halogen atoms are selectedfrom the group consisting of fluorine and chlorine, or R⁴ representsphenyl substituted by C₁ -C₁₂ -halogenoalkoxy, the halogen atoms areselected from the group consisting of fluorine and chlorine; or R⁴represents ghenyl substituted by C₁ -C₁₂ -halogenoalkylthio, the halogenatoms are selected from the group consisting of fluorine and chlorine;or R⁴ represents phenyl substituted by C₂ -C₁₂ -halogenoalkenyl, thehalogen atoms are selected from the group consisting of fluorine andchlorine; or R⁴ represents phenyl substituted by C₁ -C₄ -halogenoalkyl,the halogen atoms are selected from the group consisting of fluorine andchlorine; or R⁴ represents phenyl substituted by C₁ -C₄ -halogenoalkoxy,the halogen atoms are selected from the group consisting of fluorine andchlorine; or R⁴ represents phenyl substituted by C₁ -C₄-halogenoalkylthio, the halogen atoms are selected from the groupconsisting of fluorine and chlorine; or R⁴ represents phenyl substitutedby C₁ -C₄ -halogenoaliylsulfonyl, the halogen atoms are selected fromthe group consisting of fluorine and chlorine; or Y represents C₁ -C₄-halogenoalkylene, the halogen atoms are selected from the groupconsisting of fluorine and chlorine.
 6. A compound according to claim 4,wherein ifR⁴ represents phenyl substituted by C₁ -C₁₂ -halogenoalkoxy,the halogen atoms are selected from the group consisting of fluorine andchlorine; or R⁴ represents phenyl substituted by C₁ -C₁₂-halogenoalkylthio, the halogen atoms are selected from the groupconsisting of fluorine and chlorine; or R⁴ represents phenyl substitutedby C₂ -C₁₂ -halogenoalkenyl, the halogen atoms are selected from thegroup consisting of fluorine and chlorine; or R⁴ represents phenylsubstituted by C₁ -C₄ -halogenoalkl, the halogen atoms are selected fromthe group consisting of fluorine and chlorine; or R⁴ represents phenylsubstituted by C₁ -C₄ -halogenoalkoxy, the halogen atoms are selectedfrom the group consisting of fluorine and chlorine; or R⁴ representsphenyl substituted by C₁ -C₄ -halogenoalkylthio, the halogen atoms areselected from the group consisting of fluorine and chlorine; or R⁴represents phenyl substituted by C₁ -C₄ -halogenoalkylsulfonyl, thehalogen atoms are selected from the group consisting of fluorine andchlorine.
 7. Compositions for controlling pests, comprising apesticidally effective amount of at least one compound of the formula(I) according to claim 1 and a carrier.
 8. Method of controlling pests,comprising applying a pesticidally effective amount of a compound of theformula (I) according to claim 1 to pests and/or their environment. 9.Process for the preparation of a compound of the formula (I) accordingto claim 1, comprising:reacting a 5-aminoisothiazole of the formula (II)##STR69## in which R¹, R² and R³ have the meaning given in claim 1, withan acid halide of the formula (III)

    R.sup.4 --Y--CO--Hal                                       (III)

in which R⁴ and Y have the meaning given in claim 1 and Hal representshalogen, in the presence of a base and in the presence of a diluent; orb) acylated 5-aminoisothiazoles of the formula (Ia) ##STR70## in whichR¹, R³, R⁴ and Y have the abovementioned meaning,(α) are reacted with ahalogenating agent, if appropriate in the presence of a diluent and ifappropriate in the presence of a catalyst, or (β) are reacted with anitrating reagent, if appropriate in the presence of a diluent, or c)β-amino-thiocrotonamides of the formula (IV) ##STR71## in which R¹, R⁴and Y have the abovementioned meaning andR²⁻¹ represents cyano oralkoxycarbonyl,are cyclized with an oxidizing agent, if appropriate inthe presence of a diluent.
 10. Process for the preparation ofcompositions for controlling pests, comprising mixing a compound of theformula (I) according to claim 1 with extenders and/or surface-activeagents.